Monoamino compound and organic luminescence device using the same

ABSTRACT

A novel monoamino compound is provided. Using the monoamino compound, an organic luminescence device is provided, which exhibits a luminescence hue with extremely high purity, and having an optical output of a high luminance with a high efficiency and a long life time. The monoamino compound is represented by the following general formula [1].

TECHNICAL FIELD

The present invention relates to a monoamino compound and an organicluminescence device, and more particularly to a device that emits lightby applying an electric filed on a thin film made of an organiccompound.

BACKGROUND ART

An organic luminescence device is a device where a thin film including afluorescent organic compound is sandwiched between an anode and acathode, an electron and a hole are injected from the respectiveelectrodes to generate an exciton of the fluorescent compound, and lightwhich is emitted when the exciton returns to the ground state isutilized.

According to the study of Kodak company in 1987 (Appl. Phys. Lett. 51,913 (1987)), there has been reported a luminescence with approximately1000 cd/m² at an applied voltage of approximately 10 V in a devicehaving a separated-function type two-layer configuration using ITO as ananode, a magnesium-silver alloy as a cathode, an aluminum quinolinolcomplex as an electron-transporting material and a luminescent material,and a triphenyl amine derivative as a hole-transporting material. Therelated patents include U.S. Pat. No. 4,539,507 B, U.S. Pat. No.4,720,432 B, U.S. Pat. No. 4,885,211 B, and so on.

In addition, it is possible to generate luminescence in the range ofultraviolet to infrared lights by changing the types of the fluorescentorganic compound, and in recent years various types of compounds havebeen studied actively. For instance, it is described in U.S. Pat. No.5,151,629 B, U.S. Pat. No. 5,409,783 B, and U.S. Pat. No. 5,382,477 B,JP 2-247278 A, JP 3-255190 A, JP 5-202356 A, JP 9-202878 A, JP 9-227576A, and so on.

Furthermore, in addition to the organic luminescence device using thelow molecular weight material as mentioned above, an organicluminescence device using a conjugate polymer has been reported by agroup of the Cambridge University (Nature, 347, 539 (1990)). In thisreport, luminescence from a single layer is confirmed by the filmformation of polyphenylene vinylene (PPV) using a coating system. Therelated patents of the organic luminescence device using the conjugatepolymer include U.S. Pat. No. 5,247,190 B, U.S. Pat. No. 5,514,878 B,U.S. Pat. No. 5,672,678 B, JP 4-145192 A, JP 5-247460 A, and so on.

In this way, the recent progress in the organic luminescence device isremarkable, and the characteristics thereof suggest the possibility ofapplications for various purposes, which enable the luminescence devicewith a high luminance, a variety of luminescence wavelengths, ahigh-speed response, and a thin and lightweight form.

However, many problems still remain to be solved regarding thedurability with respect to a change with time due to a long-term usage,deterioration caused by an atmospheric gas including oxygen, moisture,or the like, and so on. Besides, in the case of considering theapplications to a full color display and so on, under the presentconditions, there are needs for an optical output of higher luminance orhigher conversion efficiency, and for luminescences of blue, green, andred having good color purity.

For instance, JP 2001-52868 A discloses a diamine compound but no blueluminescence with a high color purity (chromaticity coordinates: x,y=0.14 to 0.15, 0.09 to 0.10) has been obtained. In addition, an exampleof using a compound having a similar diamine skeleton is disclosed in JP11-312587 A. However, there has been obtained no blue luminescence witha high color purity.

DISCLOSURE OF THE INVENTION

The present invention has been made for solving such a problem inherentto the prior art and an object of the present invention is to provide anovel monoamino compound.

In addition, another object of the present invention is to provide anorganic luminescence device having a luminescence hue with an extremelyhigh purity, and also having an optical output of a high luminance witha high efficiency and a long life time.

Furthermore, another object of the present invention is to provide anorganic luminescence device which can be produced easily at acomparatively low cost.

For solving the above problems, the present inventors have finallycompleted the present invention as a result of extensive studies.

Therefore, a monoamino compound according to the present invention isrepresented by the following general formula [1]:

(where X₁ and X₂ represent divalent groups respectively selected fromthe group consisting of a substituted or unsubstituted alkylene group,aralkylene group, arylene group and heterocyclic group; and an alkylenegroup, an aralkylene group, an alkenylene group, an amino group, a silylgroup, a carbonyl group, an ether group and a thioether group, each ofwhich has a coupling group including a substituted or unsubstitutedarylene group or a divalent heterocyclic group, in which X₁ and X₂ maybe identical with or different from each other, and also X₁ and X₂ maybe directly bonded with each other;

-   -   X₃ represents a group selected from the group consisting of a        hydrogen atom, a halogen group, and substituted or unsubstituted        alkyl group, aralkyl group, aryl group, and heterocyclic group,        in which X₃ may be identical with or different from X₁ or X₂;    -   Y₁ and Y₂ represent groups respectively selected from the group        consisting of a substituted or unsubstituted alkyl group,        aralkyl group, aryl group and heterocyclic group; a substituted        or unsubstituted alkylene group, aralkylene group, alkenylene        group, amino group, and silyl group, each of which has a        coupling group including a substituted or unsubstituted arylene        group or a divalent heterocyclic group; and an unsubstituted        carbonyl group, ether group, and thioether group, each of which        has a coupling group including a substituted or unsubstituted        arylene group or a divalent heterocyclic group, in which Y₁ and        Y₂ may be identical with or different from each other;    -   Y₁ and Y₂, or X₁, Y₁, and Y₂ may be bonded with each other to        form a ring;    -   R₁ to R₈ are groups respectively selected from the group        consisting of a hydrogen atom, a halogen group, and a        substituted or unsubstituted alkyl group, aralkyl group, and        aryl group, in which R₁ to R₈ may be identical with or different        from each other; and    -   m+n denotes an integer number of 4 to 10 when all of R₁ to R₈        are hydrogen atoms, and X₁ and X₂ are directly bonded with each        other, and X₃ is a hydrogen atom, or denotes an integer number        of 1 to 10 under the other conditions.)

Further, an organic luminescence device according to the presentinvention includes at least a pair of electrodes including an anode anda cathode and one or a plurality of layers containing an organiccompound sandwiched between the pair of electrodes, in which at leastone of the layers containing the organic compound contains at least oneof the compounds represented by the general formula [1].

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a cross-sectional diagram that illustrates an example of anorganic luminescence device in accordance with the present invention.

FIG. 2 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 3 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 4 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 5 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 6 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

At first, a monoamino compound of the present invention will bedescribed.

The monoamino compound of the present invention is represented by theabove general formula [I].

The monoamino compound of the present invention can be mainly used as amaterial for an organic luminescence device, and when the compound isused as a luminescent material, a device having a high color purity, ahigh luminescence efficiency, and a long life time can be obtained evenin a single layer. In addition, a luminescence spectrum having anarrower half-value width, i.e., luminescence having a more excellentcolor purity, can be obtained by introducing a comparatively-rigidstructure such as p-phenylene skeleton into a main chain of a molecule.Furthermore, as a Stokes shift is prevented, it becomes possible toprevent the shift of a luminescence wavelength and to shift theabsorbance toward longer wavelengths. In the case of using the compoundas a dopant material, it also becomes possible to use a host materialhaving a luminescence spectrum on relatively longer wavelengths.

The monoamino compound of the present invention can be used for theobjects of both the dopant material and the host material in aluminescent layer, so that a device having a high color purity, a highluminescence efficiency, and a long life time can be obtained. Inparticular, a higher-efficient device that retains luminescence with ahigh color purity and has a higher efficiency can be obtained by the useof it as a dopant material in combination with an appropriate hostmaterial which tends to cause an energy shift.

Specific examples of substituents in the above general formula [1] willbe described below.

The substituted or unsubstituted, chain and cyclic alkyl group includesa methyl group, an ethyl group, a n-propyl group, a n-butyl group, an-hexyl group, a n-decyl group, an iso-propyl group, an iso-butyl group,a tert-butyl group, a tert-octyl group, a trifluoromethyl group, acyclohexyl group, a cyclohexylmethyl group, and the like, but the groupis not limited thereto.

The substituted or unsubstituted aralkyl group includes a benzyl group,a phenethyl group, and the like, but the group is not limited thereto.

The substituted or unsubstituted aryl group includes a phenyl group, a4-methylphenyl group, a 4-methoxyphenyl group, a 4-ethylphenyl group, a4-fluorophenyl group, a 3,5-dimethylphenyl group, a triphenylaminogroup, a biphenyl group, a terphenyl group, a naphthyl group, ananthracenyl group, a phenanthrelyl group, a pyrenyl group, a tetracenylgroup, a pentacenyl group, a fluorenyl group, a triphenylenyl group, aperylenyl group, and the like, but the group is not limited thereto.

The substituted or unsubstituted heterocyclic group includes a pyrrolylgroup, a pyridyl group, a bipyridyl group, a methylpyridyl group, aterpyrrolyl group, a thienyl group, a terthienyl group, a propylthienylgroup, a furyl group, a quinolyl group, a carbazolyl group, an oxazolylgroup, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group,and the like, but the group is not limited thereto.

The substituted or unsubstituted alkylene group includes a methylenegroup, an ethylene group, a propylene group, an iso-propylene group, abutylene group, a tert-butylene group, a hexylene group, a heptylenegroup, a cyclohexylene group, a cyclohexylmethylene group, and the like,but the group is not limited thereto.

The substituted or unsubstituted aralkylene group includes a benzylenegroup, a phenylethylene group, a phenethylene group, and the like, butthe group is not limited thereto.

The substituted or unsubstituted arylene group includes a phenylenegroup, a biphenylene group, a 2,3,5,6-tetrafluorophenylene group, a2,5-dimethylphenylene group, a naphtylene group, an anthracenylenegroup, a phenanthrenylene group, a tetracenylene group, a pentacenylenegroup, a perylenylene group, and the like, but the group is not limitedthereto.

The substituted or unsubstituted divalent heterocyclic group includes afuranylene group, a pyrrorylene group, a pyridinylene group, aterpyridinylene group, a thiophenylene group, a terthiophenylene group,an oxazolylene group, a thiazolylene group, a carbazolylene group, andthe like, but the group is not limited thereto.

The substituted or nonsubstituted alkenyl group includes a vinyl group,an allyl group (a 2-propenyl group), a 1-propenyl group, an iso-propenylgroup, a 2-butenyl group, and the like, but the group is not limitedthereto.

The substituted or unsubstituted amino group includes an amino group, amethylamino group, an ethylamino group, a dimethylamino group, adiethylamino group, a methylethylamino group, a benzylamino group, amethylbenzylamino group, a dibenzylamino group, an anilino group, adiphenylamino group, a phenyltolylamino group, a ditolylamino group, adianisolylamino group, and the like, but the group is not limitedthereto.

The substituted or unsubstituted carbonyl group includes an acetylgroup, a propionyl group, an isobutyryl group, a methacryloyl group, abenzoyl group, a naphthoyl group, an anthroyl group, a trioyl group, andthe like, but the group is not limited thereto.

The substituted or unsubstituted alkoxy group includes a methoxy group,an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a phenoxygroup, a 4-butylphenoxy group, a benzyloxy group, and the like, but thegroup is naturally not limited thereto.

The substituted or unsubstituted sulfide group includes a methylsulfidegroup, an ethylsulfide group, a phenylsulfide group, a4-methylphenylsulfide group, and the like, but the group is not limitedthereto.

As substituent groups which the above mentioned substituent groups mayhave include alkyl groups such as a methyl group, an ethyl group, an-propyl group, an iso-propyl group, a ter-butyl group, an octyl group,a benzyl group, and a phenethyl group; aralkyl groups; alkoxy groupssuch as a methoxy group, an ethoxy group, a propoxy group, a2-ethyl-octyloxy group, a phenoxy group, a 4-butylphenoxy group, and abenzyloxy group; aryl groups such as a phenyl group, a 4-methylphenylgroup, a 4-ethylphenyl group, a 3-chlorophenyl group, a3,5-dimethylphenyl group, a triphenylamino group, a biphenyl group, aterphenyl group, a naphthyl group, an anthryl group, a phenanthrylgroup, and a pyrenyl group; heterocyclic groups such as a pyridyl group,a bipyridyl group, a methylpyridyl group, a thienyl group, a terthienylgroup, a propylthienyl group, a furyl group, a quinolyl group, acarbazolyl group, and an N-ethylcarbazolyl group; halogen groups; acyano group; a nitro group; and the like, but the groups are not limitedthereto.

Next, although a typical example of the compound represented by thegeneral formula [1] will be given, the present invention is not limitedto those compounds. TABLE 1 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 1 1,0 H— Single bond Single bond

Ph Ph 2 1,0 H — Single bond Single bond

3 1,0 H —

Single bond

4 1,0 H —

Single bond

5 1,0 H — Single bond Single bond

Ph

6 1,0 H — Single bond Single bond

Ph

7 1,0 H — Single bond Single bond

Ph

8 1,0 H — Single bond Single bond

Ph

9 1,0 H — Single bond Single bond

Ph Ph 10 1,0 H — Single bond Single bond

11 1,0 H —

Single bond

12 1,0 H —

Single bond

13 1,0 H — Single bond Single bond

Ph

14 1,0 H — Single bond Single bond

Ph

15 1,0 H — Single bond Single bond

Ph

TABLE 2 R1-R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 16 1,0 H — Single bondSingle bond

Ph

17 1,0 F — Single bond Single bond

18 1,0 F — Single bond Single bond

Ph

19 1,0 F — Single bond Single bond

20 1,0 F — Single bond Single bond

Ph

21 1,0 H — Single bond Single bond

Ph Ph 22 1,0 H — Single bond Single bond

23 1,0 H — Single bond Single bond

24 1,0 H —

Single bond

25 1,0 H —

Single bond

26 1,0 H —

Single bond

27 1,0 H — Single bond Single bond

Ph

28 1,0 H — Single bond Single bond

Ph

29 1,0 H — Single bond Single bond

Ph

30 1,0 H — Single bond Single bond

Ph

TABLE 3 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 31 2,0 H — Single bondSingle bond

Ph Ph 32 2,0 H — Single bond Single bond

33 2,0 H —

Single bond

34 2,0 H — Single bond Single bond

Ph

35 2,0 H — Single bond Single bond

Ph

36 2,0 H — Single bond Single bond

Ph

37 2,0 H — Single bond Single bond

Ph

38 2,0 F — Single bond Single bond

Ph

39 2,0 F — Single bond Single bond

40 2,0 F — Single bond Single bond

Ph

41 2,0 F — Single bond Single bond

42 2,0 F — Single bond Single bond

Ph

43 2,0 F — Single bond Single bond F

44 3,0 H — Single bond Single bond

Ph Ph 45 3,0 H — Single bond Single bond

TABLE 4 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 46 3,0 H — Single bondSingle bond

47 3,0 H —

Single bond

48 3,0 H — Single bond Single bond

Ph

49 3,0 H — Single bond Single bond

Ph

50 3,0 H — Single bond Single bond

Ph

51 3,0 H — Single bond Single bond

Ph

52 3,0 H — Single bond Single bond

Ph Ph 53 3,0 H — Single bond Single bond

54 3,0 H — Single bond Single bond

Ph

55 3,0 H — Single bond Single bond

Ph

56 3,0 H — Single bond Single bond

Ph

57 3,0 H — Single bond Single bond

Ph

58 3,0 F — Single bond Single bond

59 3,0 F — Single bond Single bond

Ph

60 3,0 F — Single bond Single bond

TABLE 5 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 61 3,0 F — Single bondSingle bond

Ph

62 3,0 F — Single bond Single bond F

63 4,0 H — Single bond Single bond H

64 4,0 H — Single bond Single bond

65 4,0 H — Single bond Single bond H Ph

66 4,0 H — Single bond Single bond H Ph

67 4,0 H — Single bond Single bond H Ph

68 4,0 H — Single bond Single bond H Ph

69 4,0 H — Single bond Single bond H

70 4,0 H — Single bond Single bond H Ph

71 4,0 H — Single bond Single bond H Ph

72 4,0 H — Single bond Single bond H Ph

73 4,0 F — Single bond Single bond F

74 4,0 F — Single bond Single bond F Ph

75 5,0 H — Single bond Single bond H

TABLE 6 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 76 5,0 H — Single bondSingle bond H Ph

77 5,0 H — Single bond Single bond H Ph

78 5,0 H — Single bond Single bond H Ph

79 5,0 H — Single bond Single bond H Ph

80 5,0 H — Single bond Single bond H

81 5,0 H — Single bond Single bond H Ph

82 1,1 H F Single bond Single bond F

83 2,1 H F Single bond Single bond F

84 2,2 H F Single bond Single bond F

85 1,1 H H Single bond

H

86 1,1 H H Single bond

H

87 1,1 H H Single bond

H Ph

88 1,1 H H Single bond

H Ph

89 1,1 H H Single bond

H Ph

90 1,1 H H Single bond

H

TABLE 7 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 91 1,1 H H Single bond

H Ph

92 1,1 H H Single bond

H

93 1,1 H H Single bond

H

94 1,1 H H Single bond

H

95 1,1 H H Single bond

H

96 1,1 H H Single bond

H

97 1,1 H H Single bond

H

98 1,1 H H Single bond

H

99 1,1 H H Single bond

H Ph

100 1,1 H H Single bond

H Ph

101 1,1 H H Single bond

H Ph

102 1,1 H H Single bond

H

103 1,1 H H Single bond

H

104 1,1 H H Single bond

H

105 1,1 H H Single bond

H

TABLE 8 R1- R5- [1] m,n R4 R8 X1 X2 X3 Y1 Y2 106 1,1 H H Single bond

H

107 1,1 H H Single bond

H

108 1,1 H H Single bond

H

109 2,2 H H Single bond

H

110 2,2 H H Single bond

H

111 2,2 H H Single bond

H

112 2,2 H H Single bond

H Ph

113 2,2 H H Single bond

H Ph

114 2,2 H H Single bond

H Ph

115 2,2 H H Single bond

H

116 2,2 H H Single bond

H

117 1,1 H F Single bond

F

118 1,1 H F Single bond

F

119 1,1 H F Single bond

F

120 1,1 H H

H

121 2,2 H H

H

Next, the organic luminescence device according to the present inventionwill be described detail.

The organic luminescence device according to the present inventioncomprises at least a pair of electrodes including an anode and a cathodeand one or a plurality of layers containing an organic compoundsandwiched between the pair of electrodes, wherein at least one of thelayers containing the organic compound contains at least one of themonoamino compounds represented by the above-described general formula[1].

The layer containing the compound represented by the general formula [1]preferably contains at least one of the compounds represented by thefollowing general formulae [2] to [6]. In addition the layer containingthe compound represented by the general formula [1] is preferably aluminescent layer.

(wherein Ar₁ to Ar₃ represent groups respectively selected from thegroup consisting of a substituted or unsubstituted aryl group andheterocyclic group, in which Ar₁ to Ar₃ may be identical with ordifferent from each other, or one of them may be a hydrogen atom, asubstituted or unsubstituted alkyl group, or a substituted orunsubstituted aralkyl group; and R₉ to R₁₁ represent groups respectivelyselected from the group consisting of a hydrogen atom, a halogen group,substituted or unsubstituted alkyl group and aralkyl group, asubstituted amino group, and a cyano group.)

(wherein Ar₄ to Ar₇ represent groups respectively selected from thegroup consisting of a substituted or unsubstituted aryl group andheterocyclic group, in which Ar₄ to Ar₇ may be identical with ordifferent from each other; and R₁₂ and R₁₃ represent groups selectedfrom the group consisting of a hydrogen atom, a halogen group,substituted or unsubstituted alkyl group and aralkyl group, asubstituted amino group, and a cyano group.)

(wherein Ar₈ to Ar₁₂ represent groups respectively selected from thegroup consisting of a substituted or unsubstituted aryl group andheterocyclic group, in which Ar₈ to Ar₁₂ may be identical with ordifferent from each other; and R₁₄ represents a group selected from thegroup consisting of a hydrogen atom, a halogen group, substituted orunsubstituted alkyl group, aralkyl group, aryl group and heterocyclicgroup, a substituted amino group, and a cyano group.)

(wherein Ar₁₃ to Ar₁₆ represent groups respectively selected from thegroup consisting of a substituted or unsubstituted aryl group andheterocyclic group, in which Ar₁₃ to Ar₁₆ may be identical with ordifferent from each other, or at most three of Ar₁₃ to Ar₁₆ may be ahydrogen atom, a substituted or unsubstituted alkyl group, or asubstituted or unsubstituted aralkyl group; and R₁₅ to R₁₈ representgroups respectively selected from the group consisting of a hydrogenatom, a halogen group, substituted or unsubstituted alkyl group, aralkylgroup, aryl group and heterocyclic group, a substituted amino group, anda cyano group.)

(wherein R₁₉ and R₂₀ represent groups respectively selected from thegroup consisting of a hydrogen atom, and substituted or unsubstitutedalkyl group, aralkyl group, and aryl group, in which the R₁₉ groups orthe R₂₀ groups bonded with different fluorene groups may be identicalwith or different from each other, and R₁₉ and R₂₀ bonded with the samefluorene group may be identical with or different from each other; and

-   -   R₂₁ to R₂₄ represent groups respectively selected from the group        consisting of a hydrogen atom, a halogen group, substituted or        unsubstituted alkyl group, aralkyl group, and alkoxy group, a        substituted silyl group, and a cyano group; and p is an integer        number of 2 to 10.)

Each of the compounds represented by the general formulas [2] to [6] canbe used for the purposes of both the dopant material and the hostmaterial in a luminescent layer, so that a device having a high colorpurity, a high luminescence efficiency, and a long life time can beobtained. A device that retains luminescence with a high color purityand has a higher efficiency can be obtained by the use of a compoundrepresented by the general formula [1] as a dopant material andcombining the compound with an appropriate host material that tends tocause an energy shift, for example the compounds represented by thegeneral formulas [2] to [6]. The concentration of the dopant to the hostmaterial is preferably 0.01% by weight to 50% by weight, more preferably0.5% by weight to 10% by weight.

Specific examples of substituents in the general formulae [2] to [6] arein common with those of the above general formula [1]. The followingsare typical examples of the compounds represented by the generalformulae [2] to [6], but the present invention is not limited to thosecompounds.

Preferable examples of the organic luminescence device of the presentinvention are shown in FIGS. 1 to 6.

FIG. 1 is a cross-sectional diagram that illustrates an example of theorganic luminescence device of the present invention. In FIG. 1, thedevice comprises an anode 2, a luminescent layer 3, and a cathode 4,which are formed on a substrate 1 in that order. The luminescence deviceused herein is useful when it singly has a hole-transporting ability, anelectron-transporting ability, and a luminescence property in itself orwhen it is used in combination with compounds having thosecharacteristics.

FIG. 2 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 2, thedevice comprises an anode 2, a hole-transporting layer 5, anelectron-transporting layer 6, and a cathode 4, which are formed on asubstrate 1 in that order. In this case, a luminescent material isuseful when a material having one or both of a hole-transportingproperty and an electron-transporting property is used for therespective layers and the luminescent material is used in combinationwith a hole-transporting material or an electron-transporting materialhaving no luminescence property. In addition, in this case, theluminescent layer 3 is composed of either the hole-transporting layer 5or the electron-transporting layer 6.

FIG. 3 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 3, thedevice comprises an anode 2, a hole-transporting layer 5, a luminescentlayer 3, an electron-transporting layer 6, and a cathode 4, which areformed on a substrate 1 in that order. This is one in which acarrier-transporting function and a luminescence function are separatedfrom each other, and is used appropriately in combination with compoundshaving a hole-transporting property, an electron-transporting property,and a luminescence property, respectively. Thus, the degree of freedomin selecting a material increases extremely. In addition, various kindsof compounds having different luminescent wavelengths can be used.Therefore, it becomes possible to diversify luminescence hue.Furthermore, it also becomes possible to increase the luminescenceefficiency by effectively confining each carrier or exciton in themiddle luminescent layer 3.

FIG. 4 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 4, ascompared with the example of FIG. 3, the device is constructed such thata hole-injection layer 7 is inserted in the anode 2 side. It iseffective in the improvement of an adhesion between the anode 2 and thehole-transporting layer 5 or the improvement of an injection property ofholes, so that it is effective in lowering voltage.

FIGS. 5 and 6 are cross-sectional diagrams that illustrate otherexamples of the organic luminescence device of the present invention. Ineach of FIGS. 5 and 6, as compared with the examples of FIGS. 3 and 4,the device is constructed such that a layer (a hole-blocking layer 8)that prevents a hole or an exciton from passing toward the cathode 4side is inserted between the luminescent layer 3 and theelectron-transporting layer 6. The use of a compound having an extremelyhigh ionization-potential as the hole-blocking layer 8 allows aconfiguration effective to an improvement in luminescence efficiency.

However, in FIGS. 1 to 6, there are shown common basic deviceconfigurations. The configuration of the organic luminescence deviceusing the compound of the present invention is not limited thereto. Forinstance, it is possible to adopt various layer configurations such asone in which an insulating layer is formed at the interface between theelectrode and the organic layer, one in which an adhesive layer or aninterference layer is formed, and one in which the hole-transportinglayer is composed of two layers with different ionization potentials.

The monoamino compound represented by the general formula [1] to be usedin the present invention can be used in any modes of FIGS. 1 to 6.

In particular, an organic layer using the compound of the presentinvention is useful as a luminescent layer, an electron-transportinglayer, or a hole-transporting layer. In addition, a layer formed by avacuum deposition method, a solution-coating method, or the like hardlycauses crystallization or the like and is excellent in stability withtime.

In the present invention, in particular the monoamino compoundrepresented by the general formula [1] is used as a component of theluminescent layer. However, hole-transporting compounds, luminescentcompounds, electron-transporting compounds, or the like, which have beenknown, may be used together if required.

Examples of those compounds will be given below.Hole-transporting compound

Electron-transporting luminescent material

Luminescent material

Luminescent layer matrix material and electron-transporting material

Polymeric hole-transporting material

Polymeric luminescent material and charge-transporting material

In the organic luminescence device of the invention, the layercontaining the monoamino compound represented by the general formula [1]and the layer made of another organic compound are generally formed asthin films by a vacuum deposition method, or by a coating method afterbeing dissolved in an appropriate solvent. In particular, in the case offorming a film with a coating method, the film may be formed incombination with an appropriate binder resin.

The above binder resin can be selected from a wide variety of the binderresins including, for example, polyvinyl carbazole resin, polycarbonateresin, polyester resin, polyarylate resin, polystyrene resin, acrylicresin, methacryl resin, butyral resin, polyvinyl acetal resin, diallylphthalate resin, phenol resin, epoxy resin, silicone resin, polysulfoneresin, and urea resin, although not limited to them. In addition, thoseresins may be used solely or one or two or more resins may be combinedwith each other as a copolymer.

The anode material may be one preferably having a large work function.For example, a simple metal substance such as gold, platinum, nickel,palladium, cobalt, selenium, or vanadium, or an alloy thereof, or ametal oxide such as tin oxide, zinc oxide, indium tin oxide (ITO), orindium zinc oxide can be used. In addition, a conductive polymer such aspolyaniline, polypyrrole, polythiophene, or polyphenylene sulfide can bealso used. Those electrode substances may be used solely or two or moresubstances may be used together.

On the other hand, the cathode material may be one preferably having asmall work function. For example, a simple metal substance such aslithium, sodium, potassium, calcium, magnesium, aluminum, indium,silver, lead, tin, or chromium, or an alloy of plural substances can beused. It is also possible to use a metal oxide such as indium tin oxide(ITO). In addition, the cathode may be constructed as a single layer ormay have a multi-layer configuration.

The substance used in the present invention may be, although notparticularly limited to, a non-transparent substrate such as a metallicsubstrate or a ceramic substrate, or a transparent substrate formed ofglass, quartz, plastic sheets, or the like. In addition, it is alsopossible to control the luminescence color by using a color filter film,a fluorescent color-converting filter film, a dielectric reflectionfilm, or the like as a substrate.

Note that, a protective layer or a sealing layer may be formed on theprepared device for preventing the device from contacting with oxygen,moisture, or the like. The protective layer may be a diamond thin film;a film made of an inorganic material such as a metal oxide or a metalnitride; a polymer film made of a fluorocarbon resin, polyparaxylene,polyethylene, a silicone resin, or a polystyrene resin, or the like; orfurthermore a photo-curing resin. Furthermore, it is also possible topackage the device itself with an appropriate sealing resin whilecovering it with a glass, a gas-impermeable film, a metal, or the like.

EXAMPLES

Hereinafter, the present invention will be described more specificallywith examples. However, the present invention is not limited to thoseexamples.

Example 1 Method of Producing Exemplified

Compound No. [1]—38]

In a nitrogen flow, 160 mg (0.282 mmol) of palladiumbis(benzylideneacetone) and 170-mg (0.846 mmol) oftri-tert-butylphosphine were dissolved in 40 ml of toluene and thenstirred for 15 minutes at room temperature. Then, 0.58 g (1.27 mmol) of4,4′-dibromo-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyl dissolved in50 ml of toluene was dropped into the mixture and it was stirred for 30minutes. Furthermore, 0.34 g (1.27 mmol) ofN-(9-anthracenyl)-N-phenylamine was dissolved in 50 ml of toluene andwas then dropped therein, followed by the addition of 0.18 g (1.91 mmol)of sodium tert-butoxide. Then, the mixture was heated and stirred forabout 8 hours in an oil bath heated at 120° C. After returning thereaction solution to room temperature, 50 ml of water was added theretoand the resultant solution was then separated into an aqueous layer andan organic layer. Furthermore, the aqueous layer was extracted withtoluene and ethyl acetate, and was then combined with the previousorganic layer and dried with magnesium sulfate. The solvent wasevaporated and then the residue was purified by silicagel-columnchromatography (toluene:hexane=1:2) to obtain 0.55 g of4-bromo-4′-[N-(9-anthracenyl)-N-phenylamino]-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyl.

In a nitrogen flow, 1 g (1.55 mmol) of4-bromo-4′-[N-(9-anthracenyl)-N-phenylamino]-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyland 0.40 g (2.33 mmol) of naphthalene-1-boronic acid were dissolved andstirred in a deaerated mixture solvent of 80 ml of toluene and 40 ml ofethanol, followed by adding 23 ml of a sodium carbonate aqueous solutionprepared by dissolving 6 g of anhydrous sodium carbonate in 30 ml ofwater in a dropwise manner. After stirring the mixture for 30 minutes,135 mg (0.117 mmol) of tetrakis(triphenylphosphine)palladium was addedthereto. Then, the mixture was heated and stirred for about 3 hours inan oil bath heated at 80° C. After returning the reaction solution toroom temperature, 40 ml of water and 50 ml of ethyl acetate were addedthereto and the resultant solution was then separated into an aqueouslayer and an organic layer. Furthermore, the aqueous layer was extractedwith toluene and ethyl acetate, and was then combined with the previousorganic layer and dried with magnesium sulfate. The solvent wasevaporated and then the residue was purified by silicagel-columnchromatography (toluene:hexane=1:2) to obtain 0.90 g of the exemplifiedcompound [1]-38.

Example 2 Method of Producing the Exemplified compound No. [1]—109]

In a nitrogen flow, 1 g (2.98 mmol) of 9,10 -dibromoanthracene and 1.44g (4.46 mmol) of bis(4-methylphenyl)aminobenzene-4-boronic acid weredissolved and stirred in a deaerated mixture solvent of 100 ml oftoluene and 50 ml of ethanol, followed by dropping a sodium carbonateaqueous solution prepared by dissolving 9 g of anhydrous sodiumcarbonate in 45 ml of water. After stirring the mixture for 30 minutes,257 mg (0.223 mmol) of tetrakis(triphenylphosphine)palladium was addedthereto. Then, the mixture was heated and stirred for about 3 hours inan oil bath heated at 80° C. After returning the reaction solution toroom temperature, 40 ml of water and 50 ml of ethyl acetate were addedthereto and the resultant solution was then separated into an aqueouslayer and an organic layer. Furthermore, the aqueous layer was extractedwith toluene and ethyl acetate, and was then combined with the previousorganic layer and dried with magnesium sulfate. The solvent wasevaporated and then the residue was purified by silicagel-columnchromatography (toluene:hexane=1:2) to obtain 1.13 g of9-[bis(4-methylphenyl)amino]phenyl-10-bromoanthracene.

In a nitrogen flow, 1 g (1.89 mmol) of9-[bis(4-methylphenyl)amino]phenyl-10-bromoanthracene and 0.56 g (2.84mmol) of 1,1′-bisphenyl-4-boronic acid were dissolved and stirred in adeaerated mixture solvent of 100 ml of toluene and 50 ml of ethanol,followed by dropping a sodium carbonate, aqueous solution prepared bydissolving 6 g of anhydrous sodium carbonate in 30 ml of water. Afterstirring the mixture for 30 minutes, 164 mg (0.142 mmol) oftetrakis(triphenylphosphine)palladium was added thereto. Then, themixture was heated and stirred for about 3 hours in an oil bath heatedat 80° C. After returning the reaction solution to room temperature, 40ml of water and 50 ml of ethyl acetate were added thereto and theresultant solution was then separated into an aqueous layer and anorganic layer. Furthermore, the aqueous layer was extracted with tolueneand ethyl acetate, and was then combined with the previous organic layerand dried with magnesium sulfate. The solvent was, evaporated and thenthe residue was purified by silicagel-column chromatography(toluene:hexane=1:2) to obtain 1.04 g of the exemplified compound[1]-109.

Example 3

An organic luminescence device constructed as shown in FIG. 3 wasproduced by a method described below.

A glass substrate provided as a substrate 1, on which a film of indiumtin oxide (ITO) of 120 nm in thickness was formed as an anode 2 by asputtering method, was used as a transparent conductive supportsubstrate. This substrate was sequentially subjected to ultrasoniccleaning with acetone and isopropyl alcohol (IPA), and was then washedwith IPA by boiling, followed by drying. Furthermore, one washed withUV/ozone was used as a transparent conductive support substrate.

A chloroform solution was prepared by using a compound represented bythe following structural formula as a hole-transporting material so theconcentration of the solution would be 0.5% by weight.

This solution was dropped on the ITO electrode (the anode 2) and wasthen spin-coated at a rotation speed of 500 RPM for 10 seconds at firstand next at a rotation speed of 1000 RPM for 1 minute thereby forming athin film. Subsequently, it was dried in a vacuum oven at 80° C. for 10minutes to completely remove the solvent in the thin film. The thicknessof the resulting TPD film (the hole-transporting layer 5) was 50 nm.

Then, the above exemplified compound No. [1]-70 and the aboveexemplified compound No. [2]-50 (weight ratio of 5:100) were depositedtogether on the hole-transporting layer 5 to form a luminescent layer 3of 20 nm in thickness. The film formation was performed under theconditions of the degree of vacuum of 1.0×10⁻⁴ Pa and the rate of filmformation of 0.2 to 0.3 nm/sec.

Furthermore, aluminum quinolinol (Alq3) was formed into a film of 40 nmin thickness as an electron-transporting layer 6 by a vacuum depositionmethod. Those organic layers were deposited under the conditions of thedegree of vacuum of 1.0×10⁻⁴ Pa and the rate of film formation of 0.2 to0.3 nm/second.

Next, by using a deposition material made of an aluminum-lithium alloy(a lithium content of 1% by atom), a metal-layer film of 10 nm inthickness was formed on the organic layer described earlier by a vacuumdeposition method, and furthermore an aluminum film of 150 nm inthickness was formed thereon by a vacuum deposition method to obtain anorganic luminescence device having an aluminum-lithium alloy film as anelectron-injecting electrode (a cathode 4). The film formation wasperformed under the conditions of the degree of vacuum of 1.0×10⁻⁴ Paand the rate of film formation of 1.0 to 1.2 nm/second at the time ofdeposition.

The resulting organic EL device was covered with a protective glassplate in an atmosphere of dried air and was sealed with an acrylic resinadhesive so as to prevent the device from being deteriorated by theadsorption of moisture.

When a voltage of 8 V was applied to the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1650 cd/m², a maximum luminance of 5770 cd/m², and a luminescenceefficiency of 0.621 m/W was observed.

Examples 4 to 8

Devices were prepared in the same way as that of Example 3 except thatthe exemplified compounds shown in Table 9 were used in stead of theexemplified compound [1]-70. TABLE 9 Examplified Applied Maximum Exam-compound voltage Luminance Luminance Efficiency ple No. (V) (cd/m²)(cd/m²) (lm/W) 4 [1]-38 8 1840 6150 0.65 5 [1]-45 8 2100 7220 0.71 6[1]-86 9 1560 4900 0.53 7 [1]-100 8 2900 8300 0.82 8 [1]-109 8 2200 72700.72

Example 9

A device was prepared in the same way as that of Example 3 except thatthe above exemplified compound No. [1]-70 and the above exemplifiedcompound No. [2]-15 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 9 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1620 cd/m², a maximum luminance of 4850 cd/m², and a luminescenceefficiency of 0.55 lm/W was observed.

Example 10

A device was prepared in the same way as that of Example 9 except thatthe exemplified compound [1]-109 was used in stead of the exemplifiedcompound [1]-70.

When a voltage of 9 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1850 cd/m², a maximum luminance of 6920 cd/m², and a luminescenceefficiency of 0.66 lm/W was observed.

Example 11

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-70 and the above exemplifiedcompound No. [3]-1 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1810 cd/m², a maximum luminance of 6980 cd/m², and a luminescenceefficiency of 0.70 lm/W was observed.

Example 12

A device was prepared in the same way as that of Example 11, except thatthe exemplified compound [1]-75 was used in stead of the exemplifiedcompound [1]-70.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1870 cd/m², a maximum luminance of 7050 cd/m², and a luminescenceefficiency of 0.73 lm/W was observed.

Example 13

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-38 and the above exemplifiedcompound No. [4]-1 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (a cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of2180 cd/m², a maximum luminance of 7560 cd/m², and a luminescenceefficiency of 0.80 lm/W was observed.

Example 14

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-70 and the above exemplifiedcompound No. [5]-2 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of2800 cd/m², a maximum luminance of 7950 cd/m², and a luminescenceefficiency of 0.85 lm/W was observed.

Example 15

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-109 and the above exemplifiedcompound No. [5]-9 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of4250 cd/m², a maximum luminance of 8230 cd/m², and a luminescenceefficiency of 1.08 lm/W was observed.

Example 16

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-86 and the above exemplifiedcompound No. [6]-1 (weight ratio of 5:100) were deposited together toform a luminescent layer 3 of 20 nm in thickness.

When a voltage of 9 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of1420 cd/m², a maximum luminance of 3870 cd/m², and a luminescenceefficiency of 0.48 lm/W was observed.

Example 17

A device was prepared in the same way as that of Example 3, except thatthe above exemplified compound No. [1]-70 was deposited to form aluminescent layer 3 of 20 nm in thickness.

When a voltage of 8 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, blue luminescence with a luminescent luminance of720 cd/m², a maximum luminance of 4830 cd/m², and a luminescenceefficiency of 0.50 lm/W was observed.

Examples 18-23

The luminescence spectrums of the devices prepared in Examples 3, 10,12, 13, 14, and 15 were observed by means of MCPD-7000 andCIE-chromaticity coordinates thereof were measured. The results areshown in Table 10. TABLE 10 Example CIE-chromaticity Example of devicecoordinates (x, y) 18 3 0.15, 0.09 19 10 0.15, 0.10 20 12 0.15, 0.10 2113 0.15, 0.11 22 14 0.16, 0.10 23 15 0.15, 0.11

Example 24

When a voltage was applied to the device prepared in Example 15 in anatmosphere of nitrogen for 100 hours while retaining a current densityat 7.0 mA/cm², an initial luminance of 510 cd/m² changed to a luminanceof 450 cd/m² after 100 hours, indicating small deterioration ofluminance.

Comparative Example 1

A device was prepared in the same way as that of Example 3 except thatthe following styryl compound was used as a luminescent layer 3.

When a voltage of 10 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, green-tinged bluish white luminescence with aluminescent luminance of 120 cd/m², a maximum luminance of 3800 cd/m²,and a luminescence efficiency of 0.17 lm/W was observed.

Comparative Example 2

A device was prepared in the same way as that of Example 1, except thatthe above styryl compound and the above exemplified compound No. [4]-1(weight ratio of 5:100) were deposited together to form a luminescentlayer 3 of 20 nm in thickness.

When a voltage of 10 V was applied on the device obtained in this way,where the ITO electrode (the anode 2) was provided as a positiveelectrode and the Al—Li electrode (the cathode 4) was provided as anegative electrode, green-tinged bluish white luminescence with aluminescent luminance of 125 cd/m², a maximum luminance of 4500 cd/m²,and a luminescence efficiency of 0.30 lm/W was observed.

Comparative Example 3

The luminescence spectrum of the device prepared in Comparative Example2 was observed by means of MCPD-7000 and CIE-chromaticity coordinatesthereof were measured. As a result, (x, y)=(0, 16, 0, 30) was obtained.

As described above with reference to the embodiments and examples, theorganic luminescence device using the monoamino compound represented bythe general formula [1] of the present invention obtains, as a singlelayer or a mixed layer of dopant/host, luminescence with a highluminance at a low applied voltage, and also the color purity anddurability thereof are excellent.

Furthermore, the device can be prepared by using a vapor-depositionmethod, a casting method, or the like, and the device having a largearea can be easily prepared at a comparatively low cost.

1. A monoamino compound represented by the following general formula [1]:

(wherein X₁ and X₂ represent divalent groups respectively selected from the group consisting of a substituted or unsubstituted alkylene group, aralkylene group, arylene group and heterocyclic group; and an alkylene group, an aralkylene group, an alkenylene group, an amino group, a silyl group, a carbonyl group, an ether group and a thioether group, each of which has a coupling group including a substituted or unsubstituted arylene group or a divalent heterocyclic group, in which X₁ and X₂ may be identical with or different from each other, and also X₁ and X₂ may be directly bonded with each other; X₃ represents a group selected from the group consisting of a hydrogen atom, a halogen group, and substituted or unsubstituted alkyl group, aralkyl group, aryl group, and heterocyclic group, in which X₃ may be identical with or different from X₁ or X₂; Y₁ and Y₂ represent groups respectively selected from the group consisting of a substituted or unsubstituted alkyl group, aralkyl group aryl group and heterocyclic group; a substituted or unsubstituted alkylene group, aralkylene group, alkenylene group, amino group, and silyl group, each of which has a coupling group including a substituted or unsubstituted arylene group or a divalent heterocyclic group; and an unsubstituted carbonyl group, ether group, and thioether group, each of which has a coupling group consisting of a substituted or unsubstituted arylene group or a divalent heterocyclic group, in which Y₁ and Y₂ may be identical with or different from each other; Y₁ and Y₂, or X₁, Y₁, and Y₂ may be bonded with each other to form a ring; R₁ to R₈ represent groups respectively selected from the group consisting of a hydrogen atom, a halogen group, and a substituted or unsubstituted alkyl group, aralkyl group, and aryl group, in which R₁ to R₈ may be identical with or different from each other; and m+n denotes an integer number of 4 to 10 when all of R₁ to R₈ are hydrogen atoms, and X₁ and X₂ are directly bonded with each other, and X₃ is a hydrogen atom, or denotes an integer number of 1 to 10 under the other conditions.)
 2. An organic luminescence device comprising at least a pair of electrodes including an anode and a cathode and one or a plurality of layers containing an organic compound sandwiched between the pair of electrodes, wherein at least one of the layers containing the organic compound contains at least one of compounds represented by the following general formula [1]:

(wherein X₁ and X₂ represent divalent groups respectively selected from the group consisting of a substituted or unsubstituted alkylene group, aralkylene group, arylene group and heterocyclic group; and an alkylene group, an aralkylene group, an alkenylene group, an amino group, a silyl group, a carbonyl group, an ether group and a thioether group, each of which has a coupling group including a substituted or unsubstituted arylene group or a divalent heterocyclic group, in which X₁ and X₂ may be identical with or different from each other, and also X₁ and X₂ may be directly bonded with each other; X₃ represents a group selected from the group consisting of a hydrogen atom, a halogen group, and substituted or unsubstituted alkyl group, aralkyl group, aryl group, and heterocyclic group, in which X₃ may be identical with or different from X₁ or X₂; Y₁ and Y₂ represent groups respectively selected from the group consisting of a substituted or unsubstituted alkyl group, aralkyl group, aryl group and heterocyclic group; a substituted or unsubstituted alkylene group, aralkylene group, alkenylene group, amino group, and silyl group, each of which has a coupling group including a substituted or unsubstituted arylene group or a divalent heterocyclic group; and an unsubstituted carbonyl group, ether group, and thioether group, each of which has a coupling group including a substituted or unsubstituted arylene group or a divalent heterocyclic group, in which Y₁ and Y₂ may be identical with or different from each other; Y₁ and Y₂, or X₁, Y₁, and Y₂ may be bonded with each other to form a ring; R₁ to R₈ represent groups respectively selected from the group consisting of a hydrogen atom, a halogen group, and a substituted or unsubstituted alkyl group, aralkyl group, and aryl group, in which R₁ to RB may be identical with or different from each other; and m+n denotes an integer number of 4 to 10 when all of R₁ to R₈ are hydrogen atoms, and X₁ and X₂ are directly bonded with each other, and X₃ is a hydrogen atom, or denotes an integer number of 1 to 10 under the other conditions.)
 3. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] contains at least one of the compounds represented by the following general formula [2]:

(wherein Ar₁ to Ar₃ represent groups respectively selected from the group consisting of a substituted or unsubstituted aryl group and heterocyclic group, in which Ar₁ to Ar₃ may be identical with or different from each other, or one of them may be a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group; and R₉ to R₁₁ represent groups respectively selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl group and aralkyl group, a substituted amino group, and a cyano group.)
 4. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] contains at least one of the compounds represented by the following general formula [3]:

(wherein Ar₄ to Ar₇ represent groups respectively selected from the group consisting of a substituted or unsubstituted aryl group and heterocyclic group, in which Ar₄ to Ar₇ may be identical with or different from each other; and R₁₂ and R₁₃ represent groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl group and aralkyl group, a substituted amino group, and a cyano group.)
 5. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] contains at least one of the compounds represented by the following general formula [4]:

(wherein Ar₈ to Ar₁₂ represent groups respectively selected from the group consisting of a substituted or unsubstituted aryl group and heterocyclic group, in which Ar₈ to Ar₁₂ may be identical with or different from each other; and R₁₄ represents a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl group, aralkyl group, aryl group and heterocyclic group, a substituted amino group, and a cyano group.)
 6. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] contains at least one of the compounds represented by the following general formula [5]:

(wherein Ar₁₃ to Ar₁₆ represent groups respectively selected from the group consisting of a substituted or unsubstituted aryl group and heterocyclic group, in which Ar₁₃ to Ar₁₆ may be identical with or different from each other, or at most three of Ar₁₃ to Ar₁₆ may be a hydrogen atom, a substituted or unsubstituted alkyl group,- or a substituted or unsubstituted aralkyl group; and R₁₅ to R₁₈ represent groups respectively selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl group, aralkyl group, aryl group and heterocyclic group, a substituted amino group, and a cyano group.)
 7. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] contains at least one of the compounds represented by the following general formula [6]:

(wherein R₁₉ and R₂₀ represent groups respectively selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl group, aralkyl group, and aryl group, in which the R₁₉ groups or the R₂₀ groups bonded with different fluorene groups may be identical with or different from each other, and R₁₉ and R₂₀ bonded with the same fluorene group may be identical with or different from each other; and R₂₁ to R₂₄ represent groups respectively selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl group, aralkyl group, and alkoxy group, a substituted silyl group, and a cyano group; and p is an integer number of 2 to 10.)
 8. An organic luminescence device according to claim 2, wherein the layer containing the compound represented by the general formula [1] is provided as a luminescent layer. 